Structure-forming properties of 3-furylpropenoic acid derivatives in solution and in the solid state

Kiss T., János and Felföldi, Károly and Paksi, Z. and Pálinkó, István (2003) Structure-forming properties of 3-furylpropenoic acid derivatives in solution and in the solid state. JOURNAL OF MOLECULAR STRUCTURE, 651-53. pp. 253-258. ISSN 0022-2860

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Abstract

Measurements by infrared (FT-IR) spectroscopy in the solid state as well as in solution and molecular modeling calculations revealed that the major structure forming force (short range ordering) between 2-phenyl-3(2'-furyl)propenoic acid stereoisomers, was the C=O...H-O intermolecular hydrogen bonding between the carboxylic groups. For the E isomer no other secondary intermolecular interaction could be measured nor calculated. Molecular modeling showed that long-range ordering was possible between the hydrogen-bonded dimers of the Z isomer via (phenyl)C-H...(furyl)O close contacts. The methyl esters also had short-range ordering through (phenyl)C-H...(carbonyl)O interaction, while only the Z isomer offered the possibility of long-range order. Chain-like structures were formed via (phenyl)C-H...(furyl)O hydrogen bonds.

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